ATE377583T1 - METHOD FOR ISOLATION, PURIFICATION AND FORMULATION OF A STABLE COMMERCIAL LUTE PASTE MADE OF OLEORESIN - Google Patents
METHOD FOR ISOLATION, PURIFICATION AND FORMULATION OF A STABLE COMMERCIAL LUTE PASTE MADE OF OLEORESINInfo
- Publication number
- ATE377583T1 ATE377583T1 AT05726218T AT05726218T ATE377583T1 AT E377583 T1 ATE377583 T1 AT E377583T1 AT 05726218 T AT05726218 T AT 05726218T AT 05726218 T AT05726218 T AT 05726218T AT E377583 T1 ATE377583 T1 AT E377583T1
- Authority
- AT
- Austria
- Prior art keywords
- oleoresin
- lutein
- filtration
- alcohol
- lute
- Prior art date
Links
- 239000008601 oleoresin Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 238000009472 formulation Methods 0.000 title 1
- 238000002955 isolation Methods 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 238000000746 purification Methods 0.000 title 1
- 235000012680 lutein Nutrition 0.000 abstract 4
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 abstract 4
- 229960005375 lutein Drugs 0.000 abstract 4
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 abstract 4
- 239000001656 lutein Substances 0.000 abstract 4
- 239000007787 solid Substances 0.000 abstract 4
- KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 abstract 4
- FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 238000001914 filtration Methods 0.000 abstract 3
- -1 Xanthophylls esters Chemical class 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 239000013078 crystal Substances 0.000 abstract 2
- 235000008210 xanthophylls Nutrition 0.000 abstract 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 238000003556 assay Methods 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000003456 ion exchange resin Substances 0.000 abstract 1
- 229920003303 ion-exchange polymer Polymers 0.000 abstract 1
- 239000003444 phase transfer catalyst Substances 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
- C07C403/24—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by six-membered non-aromatic rings, e.g. beta-carotene
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
- A23L5/40—Colouring or decolouring of foods
- A23L5/42—Addition of dyes or pigments, e.g. in combination with optical brighteners
- A23L5/43—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives
- A23L5/44—Addition of dyes or pigments, e.g. in combination with optical brighteners using naturally occurring organic dyes or pigments, their artificial duplicates or their derivatives using carotenoids or xanthophylls
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B61/00—Dyes of natural origin prepared from natural sources, e.g. vegetable sources
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention relates to a process for obtaining stabilized Lutein with about 95% yield from oleoresin at ambient temperature, said process comprising steps of dissolving cleaned oleoresin in alcohol to obtain dissolved Xanthophylls esters as clear solution on filtration, cleaning dissolved oleoresin comprising xanthophylls esters in ion-exchange resin, hydrolyzing the clear solution with base in presence of phase-transfer catalyst in alcohol medium, quenching the hydrolyzed solution in water maintaining acidic pH to obtain undissolved solids on filtration, dissolving the solids in ester to obtain ester layer on filtration, drying ester layer to obtain semi-solid residue, triturating the semi-solid residue in alcohol whereby obtaining lutein crystals of about 65% assay and an alcoholic fraction, distilling the alcoholic fraction to obtain non water-soluble fractions, and mixing the Lutein crystals with non water-soluble fractions to obtain a stable Lutein paste.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53704204P | 2004-01-16 | 2004-01-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE377583T1 true ATE377583T1 (en) | 2007-11-15 |
Family
ID=34794440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT05726218T ATE377583T1 (en) | 2004-01-16 | 2005-01-17 | METHOD FOR ISOLATION, PURIFICATION AND FORMULATION OF A STABLE COMMERCIAL LUTE PASTE MADE OF OLEORESIN |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7179930B2 (en) |
| EP (1) | EP1704134B1 (en) |
| JP (1) | JP4001615B2 (en) |
| KR (1) | KR100782434B1 (en) |
| CN (1) | CN100381414C (en) |
| AT (1) | ATE377583T1 (en) |
| AU (1) | AU2005205250B2 (en) |
| CA (1) | CA2544902C (en) |
| DE (1) | DE602005003201T2 (en) |
| DK (1) | DK1704134T3 (en) |
| ES (1) | ES2294694T3 (en) |
| PT (1) | PT1704134E (en) |
| RU (1) | RU2321582C2 (en) |
| WO (1) | WO2005068409A1 (en) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7829126B2 (en) * | 2005-10-26 | 2010-11-09 | Abbott Laboratories | Infant formulas containing docosahexaenoic acid and lutein |
| US20070166354A1 (en) | 2005-10-26 | 2007-07-19 | Bridget Barrett-Reis | Method of reducing the risk of retinopathy of prematurity in preterm infants |
| AT503329A1 (en) * | 2006-03-02 | 2007-09-15 | Omnica Gmbh | PROCESS FOR PREPARING A COMPOSITION CONTAINING AT LEAST ONE XANTOPHYLL |
| ES2318992B1 (en) * | 2006-09-18 | 2009-12-28 | Carotenoid Technologies, S.A. | PROCEDURE FOR THE PREPARATION OF ESSENTIALLY PURE LUTEINE FROM MARIGOLD EXTRACTS. |
| CN101838229B (en) * | 2009-03-19 | 2014-05-14 | 华北制药集团新药研究开发有限责任公司 | Method for separating and purifying all-trans xanthophyl powder |
| US8716533B2 (en) | 2009-05-29 | 2014-05-06 | Kalamazoo Holdings, Inc. | Methods of saponifying xanthophyll esters and isolating xanthophylls |
| US8247615B2 (en) | 2010-05-14 | 2012-08-21 | Kalamazoo Holdings, Inc. | Process of converting esterified xanthophylls from Capsicum to non-esterified xanthophylls in high yields and purities |
| WO2011145112A1 (en) | 2010-05-17 | 2011-11-24 | Dynadis Biotehc (India) Private Limited | Process for isolation and purification of carotenoids |
| EP2593516A4 (en) * | 2010-07-13 | 2014-03-05 | Rfi Llc | ENHANCED NATURAL COLORS |
| US9458476B2 (en) | 2011-04-18 | 2016-10-04 | R.J. Reynolds Tobacco Company | Method for producing glycerin from tobacco |
| MX353630B (en) * | 2011-08-26 | 2018-01-22 | Ptt Global Chemical Public Co Ltd | Method of extracting lutein/xanthophylls from natural materials and highly purified lutein/xanthophylls obtained from the method thereof. |
| CN102887848A (en) * | 2012-10-30 | 2013-01-23 | 长沙芬康生物科技有限公司 | Method for preparing lutein crystals from marigold ointment by catalytic saponification |
| RU2649618C2 (en) | 2012-12-19 | 2018-04-04 | Новас Интернэшнл Инк. | Xanthophyll compositions and methods for use thereof |
| US9289011B2 (en) * | 2013-03-07 | 2016-03-22 | R.J. Reynolds Tobacco Company | Method for producing lutein from tobacco |
| FR3003872B1 (en) * | 2013-03-29 | 2017-02-10 | Roquette Freres | PROCESS FOR STABILIZING OXIDATION-SENSITIVE METABOLITES PRODUCED BY MICROALGUES OF THE GENUS CHLORELLA |
| CN103262931B (en) * | 2013-05-23 | 2015-09-30 | 云南瑞宝生物科技有限公司 | The hard candy of water-soluble lutein ester, its preparation method and containing water-soluble lutein ester |
| US9265284B2 (en) | 2014-01-17 | 2016-02-23 | R.J. Reynolds Tobacco Company | Process for producing flavorants and related materials |
| US10881133B2 (en) | 2015-04-16 | 2021-01-05 | R.J. Reynolds Tobacco Company | Tobacco-derived cellulosic sugar |
| US10499684B2 (en) | 2016-01-28 | 2019-12-10 | R.J. Reynolds Tobacco Company | Tobacco-derived flavorants |
| US11154087B2 (en) | 2016-02-02 | 2021-10-26 | R.J. Reynolds Tobacco Company | Method for preparing flavorful compounds isolated from black liquor and products incorporating the flavorful compounds |
| US11091446B2 (en) | 2017-03-24 | 2021-08-17 | R.J. Reynolds Tobacco Company | Methods of selectively forming substituted pyrazines |
| RU2750150C1 (en) * | 2020-07-17 | 2021-06-22 | Федеральное государственное автономное образовательное учреждение высшего образования "Северо-Восточный федеральный университет имени М.К.Аммосова" | Method for producing stable lutein paste based on vegetable cryo raw materials with increased carotenoid content |
| CN114957071A (en) * | 2021-02-25 | 2022-08-30 | 内蒙古昶辉生物科技股份有限公司 | Method for preparing lutein by marigold ointment |
| CN114957072A (en) * | 2021-02-25 | 2022-08-30 | 内蒙古昶辉生物科技股份有限公司 | Method for preparing zeaxanthin and zeaxanthin pellet from marigold ointment |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB555636A (en) | 1941-11-25 | 1943-09-01 | Richard Lant | Improvements in and relating to the treatment of vegetable seeds and particularly to the treatment of soya beans |
| US5382714A (en) | 1994-03-17 | 1995-01-17 | The Catholic University Of America | Process for isolation, purification, and recrystallization of lutein from saponified marigold oleoresin and uses thereof |
| US5648564A (en) | 1995-12-21 | 1997-07-15 | Kemin Industries, Inc. | Process for the formation, isolation and purification of comestible xanthophyll crystals from plants |
| US5876782A (en) | 1997-05-14 | 1999-03-02 | Kemin Industries, Inc. | Method for the conversion of xanthophylls in plant material |
| US6262284B1 (en) * | 1998-10-21 | 2001-07-17 | University Of Maryland | Process for extraction and purification of lutein, zeaxanthin and rare carotenoids from marigold flowers and plants |
| US6504067B1 (en) | 1999-11-24 | 2003-01-07 | Industrial Organica S.A. De C.V. | Process to obtain xanthophyll concentrates of high purity |
| WO2002060864A1 (en) * | 2001-01-30 | 2002-08-08 | Sabinsa Corporation | Process of obtaining compositions of stable lutein and lutein derivatives |
| US6380442B1 (en) | 2001-10-10 | 2002-04-30 | Bioactives, Llc | Process for the isolation of mixed carotenoids from plants |
-
2005
- 2005-01-17 WO PCT/IN2005/000016 patent/WO2005068409A1/en not_active Ceased
- 2005-01-17 ES ES05726218T patent/ES2294694T3/en not_active Expired - Lifetime
- 2005-01-17 DE DE602005003201T patent/DE602005003201T2/en not_active Expired - Fee Related
- 2005-01-17 RU RU2006116475/04A patent/RU2321582C2/en not_active IP Right Cessation
- 2005-01-17 AU AU2005205250A patent/AU2005205250B2/en not_active Ceased
- 2005-01-17 JP JP2006548589A patent/JP4001615B2/en not_active Expired - Fee Related
- 2005-01-17 EP EP05726218A patent/EP1704134B1/en not_active Expired - Lifetime
- 2005-01-17 PT PT05726218T patent/PT1704134E/en unknown
- 2005-01-17 CA CA002544902A patent/CA2544902C/en not_active Expired - Fee Related
- 2005-01-17 CN CNB2005800008869A patent/CN100381414C/en not_active Expired - Fee Related
- 2005-01-17 DK DK05726218T patent/DK1704134T3/en active
- 2005-01-17 KR KR1020067009704A patent/KR100782434B1/en not_active Expired - Fee Related
- 2005-01-17 AT AT05726218T patent/ATE377583T1/en not_active IP Right Cessation
- 2005-01-18 US US11/038,564 patent/US7179930B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007517863A (en) | 2007-07-05 |
| EP1704134A1 (en) | 2006-09-27 |
| ES2294694T3 (en) | 2008-04-01 |
| US7179930B2 (en) | 2007-02-20 |
| CN100381414C (en) | 2008-04-16 |
| DE602005003201T2 (en) | 2008-11-06 |
| WO2005068409A1 (en) | 2005-07-28 |
| CN1860091A (en) | 2006-11-08 |
| KR100782434B1 (en) | 2007-12-05 |
| RU2321582C2 (en) | 2008-04-10 |
| DE602005003201D1 (en) | 2007-12-20 |
| AU2005205250A1 (en) | 2005-07-28 |
| DK1704134T3 (en) | 2008-01-28 |
| JP4001615B2 (en) | 2007-10-31 |
| CA2544902C (en) | 2008-02-05 |
| PT1704134E (en) | 2007-12-28 |
| US20050182280A1 (en) | 2005-08-18 |
| EP1704134B1 (en) | 2007-11-07 |
| RU2006116475A (en) | 2007-11-20 |
| AU2005205250B2 (en) | 2008-11-13 |
| KR20060090272A (en) | 2006-08-10 |
| CA2544902A1 (en) | 2005-07-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |